


First Kiss

by CosmicBrownie



Series: The Hargreeves Kids (Pre-Season One Fics) [1]
Category: The Umbrella Academy (TV)
Genre: Blowjobs, Eventual Smut, F/M, Fluff, Fluff and Smut, Hair-pulling, Oral Sex, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-06-28
Updated: 2020-07-05
Packaged: 2021-03-04 00:33:32
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 4,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24954601
Author URL: https://archiveofourown.org/users/CosmicBrownie/pseuds/CosmicBrownie
Summary: She hoped they’d kiss again. And again. And again. She hoped that someday soon, they’d be in her room kissing, and there would be no one else in the world but them, no stupid academy, and they’d just make out. They’d make out for hours and he’d run one of his soft hands through her long dark hair and one up her shirt and-Oh.She liked thinking about that.
Relationships: Number Five | The Boy & Vanya Hargreeves, Number Five | The Boy/Vanya Hargreeves, Vanya Hargreeves/Vanya Hargreeves
Series: The Hargreeves Kids (Pre-Season One Fics) [1]
Series URL: https://archiveofourown.org/series/1892047
Comments: 2
Kudos: 160





	1. Magical and Beautiful

Vanya felt like she was floating. The world was merely an afterthought now as she drifted mindlessly through her day, from the study to the dining room to then her bedroom that night. All day she felt sleepy, and then that night when she went to bed, she was wide awake.

She stared up at her ceiling, grinning and sinking into her soft pillow. She played with her hair, trying in vain to drift to sleep.

Why was she feeling this way? Well, all day, her mind was on a small moment she shared in the study that morning. Ever since that morning, her heart had begun doing backflips. Ever since that morning, a blush covered her cheeks and a smile rest on her lips.

Because that morning...she and Five had finally kissed. Months ago they admitted their feelings for each other, but that morning, as they chatted in the study, Five just leaned in and kissed her. It was magical, and beautiful, and short, but still much so magical and beautiful it didn’t matter.

She turned over in her bed thinking about it. It was everything she ever dreamed of. Five was everything she’d ever dreamed of. She squealed into her pillow. 

Vanya hoped they’d do something like that again. She was glad he was finally pursuing a physical relationship with her. Leading up to that, Vanya was too afraid to make a move on her own, and too shy to ask him, so she was growing worried that it would never happen, or that he didn’t want to touch her intimately. 

There were so many nights that they’d huddled close, he’d snuck into her room or her into his, and they’d shared the whole night together lying in bed. There were times when she’d be talking, and he’d just be staring at her like she was a sunset, and she’d think “Please just kiss me.” But it wouldn’t happen. 

So this morning was cause for celebration for a number of reasons. 

She hoped they’d kiss again. And again. And again. She hoped that someday soon, they’d be in her room kissing, and there would be no one else in the world but them, no stupid academy, and they’d just make out. They’d make out for hours and he’d run one of his soft hands through her long dark hair and one up her shirt and-

Oh.

She liked thinking about that.

Vanya reached her hand under the waistband of her pajamas. Her fingers nervously crept farther down, in between her legs. Her breath hitched.

She thought about Five reaching his hand under her shirt and cupping her over her bra. He’d whisper into her ear, nipping her earlobe as he unbuttoned her shirt slowly, button by button until she was exposed. Vanya did the same as she under her pajama shirt, splaying it open.

She thought about his mouth on her neck as he reached his hands behind her and undid her bra in one swift movement. She thought about the way those hands would travel down her skirt and his fingers would dive between her legs.

Vanya kicked the heavy blanket off, shoving the waistband of her pants down and imagined Fives fingers were the ones rubbing against her, stroking against her sensitive clit. She imagined how he would take his other hand, like Vanya did, and squeeze her breasts and toy with her hard nipples.

She thought about how he would feel tucking his gentle fingers inside her. How he’d curl them up and hit find her sensitive spot and never give her a break as he built her up and up until she was shamelessly moaning his name into his mouth between short gasps, until-

-she barely heard the sound of Five teleport to her bedside, nor did she see the flash of light as he appeared. But she did peek her eyes open, to find Five turning around and looking at the scene before him a moment later.

As she took a moment to register, so did Five. His eyes widened as she yelped and dove into her covers, covering herself in an instant.

“I-V-Vanya-“ he stuttered.

She covered her face, her already blushing cheeks now bright, hot red. She tucked herself tighter into her ball of embarrassment. “Hi.” she squeaked, her voice muffled in her blanket.

Five swallowed. “Were you-“

She didn’t say anything, to which he replied “Sorry. Bad timing. I’ll just-go.”

Vanya heard that same sparking sound and faintly saw a flash of light to indicate he had left. She waited there in her ball for several minutes though before she peeled out to see nothing but darkness.

She sighed. Tomorrow morning was going to be fun.


	2. Florida

**Summary for the Chapter:**

> Vanya looked away. “W-what are you doing here? Aren’t you meant to be on that mission?”
> 
> “Yeah.” Five said, casually. “I am.”

Early that morning, before it was even light outside, the academy was called to the coast of Florida to handle a radioactive threat coming from the ocean. Even her father went with them. Vanya, of course, stayed home, as always.

She thanked her lucky stars that she didn’t have to face Five that morning though. She instead came down for breakfast late and ate with Grace, and even Pogo, who didn’t normally join them for breakfast, but thought Vanya looked lonely speaking to only Grace, so he came in and asked about her violin, to which they got a conversation started.

“But I’d really like it if I could possibly perform it...you know, for the whole family.” she said to him in regards to the song she’d been learning. “I’ve been practicing it for months now, and I think it’s pretty good. Could I perform some of my songs soon?”

Grace, expressionless, smiled at her and hummed “That sounds like a wonderful idea, Vanya.”

She beamed back at her mother, then turned. “What do you think, Pogo?” she asked happily.

Pogo smiled and gently replied “We’d all love to hear it, Miss Vanya.”

Then his eyes seemed to tell a different story, as if he knew how hopeless the idea was. “But it might be too difficult for Mr. Hargreeves to make any time in the next couple weeks. You know how he’s increased your siblings trainings difficulty and hired the new personal trainers.”

She looked down at her lap. She didn’t try to disguise her sadness this time, for how frequently she’d had to do so recently, from her friend, her violin teacher, being fired for being late, to how many missions her siblings had been going on in the past couple months. At least it never sedated her feelings for Five, or his for her. 

But it was making her miss him, and it worried her. He was always off seeing the world, and meeting other kids. She worried he’d lose interest in her. But he never did.

Suddenly, she picked up on a familiar sound in the distance. That familiar crackle that came with Five when he micro-jumped. But that didn’t make sense...

She sighed, scooting her chair back and heading toward the stairs. “I’m going to go practice anyway.” she said as she left, disappointed still, but now curious.

She made it halfway up the stairs when she bumped into Five, standing at the landing, looking at his pocket watch.

At first, she sat staring at him with wide eyes. Then she spoke. “Five?”

He looked out of breath, and his shaking fists were clutched in a way similar to when he was jumping. He cocked an eyebrow sharply and twisted his head around to face her. When he saw Vanya, he smiled, expression softening. “Hey.” he sighed. “Good morning.”

She looked away. “W-what are you doing here? Aren’t you meant to be on that mission?”

“Yeah.” he said, casually. “I am.”

“Then, what are you...”

He jumped down a couple steps. “I couldn’t wait a couple days to see you again and make things right.” His voice grew quieter with every step he took toward Vanya. “I tried to fake sick when I was called this morning, but the old man brought Grace in and caught my lie. So I tried to get out of the mission, but he wouldn’t let me.”

“But you love missions.” she muttered quietly. She looked up into his big blue eyes. “Don’t pretend you don’t. I know you live for it despite how much you hate the academy.”

He smiled. “You know me. But then when he said we’d be in Florida for a few days, I couldn’t go. So I...well.” he didn’t finish his sentence.

“Jumped all the way here from the airport?” she asked, surprised. “Really?” she asked when he nodded.

“Lots and lots of little jumps.” he laughed. “Stopped for directions too. Almost got mobbed by a gaggle of fangirls too.”

“For me?” Vanya blushed, giggling.

He put his hands in his pockets shyly, and nodded. He spoke seriously, looking deep into her eyes as he responded “I couldn’t let time fix last night. Look...I’ve been thinking about it.”

She clutched her arm nervously. “Oh...um.”

He grabbed her hand, now standing right in front of her. “I’m really sorry, V. I didn’t mean to just barge in. I should’ve knocked. Look, I can stop jumping in on you if you want-“

“No, I’m sorry. I’m just...I mean, it would probably be a good idea to knock. But you don’t have to apologize. I...” she bit her lip, not looking him in the eyes. Her voice grew quieter and quieter, until she was silent, looking down and burning holes into her shoes with her gaze.

Five grabbed her chin gently. He tilted her head up until they were face to face, centimeters apart. Slowly, he pressed a soft, tender kiss to her lips.

She smiled into it, interlacing their fingers and closing her eyes. She felt his other hand gently grabbing the side of her face, his thumb caressing her cheek. When he broke apart, he pressed their foreheads together.

“Forgive me...?” he whispered.

She nodded. “Of course. We’re totally okay.”


	3. Handkerchief

**Summary for the Chapter:**

> She set her bow and violin in their open case, then settled beside her brother. “It’s alright, Five.”
> 
> He looked at her. “So...we’re alright? Like, last night...” he began.
> 
> She blushed. They were back to this again. “Yeah.”
> 
> “So, can I now ask...what you were doing?” he asked, smiling cheekily.

Vanya didn’t notice Five come in when she was playing later.

Fueling her discouragement from that mornings conversation into passion as she played her solo alone in her room, she was so in touch with her playing, she didn’t hear Five warp right behind her, and she didn’t notice until after she had finished playing that he was there.

When she relaxed her shoulders, opening her eyes and setting her stiffened arms down, she gasped when she saw Five admiring her from the bed. 

“Five!” she laughed, coming down from her shock. “How long have you been there?”

“I think I came in right about the middle. I know I said I’d stop warping in without asking. But I heard your violin, and I wasn’t going to disturb your piece by knocking, and I assumed you were fully dressed this time.” he laughed slightly with his explanation.

She set her bow and violin in their open case, then settled beside her brother. “It’s alright, Five.”

He looked at her. “So...we’re alright? Like, last night...” he began.

She blushed. They were back to this again. “Yeah.”

“So, can I now ask...what you were doing?” he asked, smiling cheekily.

Vanya turned away, the blush coating her cheeks now vivid on her smiling face. Her hands fiddled nervously. “Five!”

“What?”

“I think you know...” she chirped meekly, in a voice that said she wasn’t going to say it out loud.

He tilted his head. “I suppose I do. But I was just wondering...what it was..” he said, going quieter. He leaned in to her, tucking the loose strands of hair in front of her ear behind it.

He whispered in to her “...what it was you were thinking about.”

Vanya but her lip, hands now clutching the sheets tight. With Five’s breath against her ear and his voice low and quiet asking what she was getting off to last night, what she was thinking about...well, she couldn’t lie.

“I think...” she said, turning to face him. “You also know the answer to that.” Her eyes had a flash of both danger and lust, a brave new emotion for Vanya.

He cocked an eyebrow. “Do I? Can I get a hint?”

“Hm...” she said, pretending to think. “Well, you know him quite well. You could say that the two of you are very close.”

He turned on the bed to face her better. “Oh, is that so?”

She nodded, her desire taking over as she desperately dove in to plant a kiss on his parted lips. He accepted it instantly, wrapping his hand around the back of her neck. She hummed into his mouth, which earned her a smile from Five.

She broke away with a short gasp. “I was thinking about you, Five. I was thinking about us...doing thing. Doing bad things.”

Five smirked as he took off his blazer and placed a hand on her knee. “Tell me more.”

She looked down at the hand that was very, ever so slightly, moving upwards on her thigh. “I thought about you undressing me...doing things to me.” she breathed out, quiet and timid.

He rubbed his hands up and down the inside of her thigh, which ignited a shiver in Vanya. He leaned in and whispered “Doing what things? Tell me about them.” He placed a kiss on her cheek, then her jaw, and traveled down to her neck, sending Vanya trembling and whimpering quietly.

“Mm, you were, uh, running your hands through my hair. And you were taking off all of my clothes. And you were touching me, so good.” she whispered into his neck.

Five murmured in agreement as his hand traveled up and up her thigh until he had reached her underwear, where he gently began to creep his hand outside the fabric, touching her through her underwear. 

“This okay?” he murmured into her neck. She whimpered weakly “Yeah.”

“What else did I do in your imagination, V?” he said with a tone in which you could hear his smirk. Vanya closed her eyes and tried to focus on that question even as Five slowly began to rub her outside of her underwear.

“You were...playing with my b-breasts.” she said, which Five seemed to like. “Your fingers were deep inside me, your mouth was on my neck, and I w-was saying your n-ah!” 

Five suddenly dove into her lips, interrupting her thought. He broke away again quickly though, saying “Sorry. I just looked at you and, well, you’re really beautiful Vanya.”

She blushed, kissing him again.

Five pressed their foreheads together like before, whispering quietly to her. “Do you want to do this?”

She looked deep into his eyes, where she was met with slight concern but a lot of lustful eagerness to outweigh it. There was no one here but the two of them. No Reginald, no academy, nobody. 

She nodded, not breaking eye contact as she changed her position on the bed. She sat back against her pillows, motioning for Five to join her. He crawled up beside her on the bed, kicking off his shoes.

She took off her shoes and blazer, intensely aware of Five’s gaze. Next she swiftly untucked her shirt and removed her sweater and tie.

Five’s hand rested on her belly, traveling up her shirt. He took his time feeling her buttons as Vanya grew more and more restless about his presence so close to her bra. She hoped this would match her fantasy.

Five looked at Vanya as his hands grabbed at her top button. “Yeah?”

“Yeah.”

He slowly undid the first button, then the next, then grew in speed with every button. Quickly, Vanya’s exposed chest came into view, her black bra a contrast to her pale skin.

Five stared for a moment, transfixed. Vanya blushed. “I know it might not be everything you hoped for...” she mumbled, to which Five immediately kissed her. “Vanya, you are everything I could have ever hoped for.”

She smiled sweetly. “Okay. Then do you want to get this off of me?”

“I thought you’d never ask.” Five breathed out, lustful and thankful.

He reached his hands back, feeling up and down her spine before reaching the latches on the back of her bra. He felt around for a moment before figuring it out and undoing the latch.

Vanya pulled the bra off herself, shyly stripping before Five’s hungry and beautifully wide eyes. He sat for a while, just staring at her, which made Vanya impatient, so she grabbed his hand and brought it to her now bare chest.

He followed her lead, taking one of her breasts in his hand. He bit his lip, groaning “Vanya, you’re so pretty. God. And you’re so soft.”

His thumb stroked over her hardening nipple, which earned him an aroused gasp from Vanya, who arched into his touch.

“Mm, you like that?” he asked. He squeezed her breasts harder and brushed his fingers against her nipples. She moaned in response, gluing her eyes shut as she writhed with every pinch and touch.

“You’re so sensitive.” he breathed out. “Jesus. You’re beautiful.”

Five leaned down and planted a kiss on her tits. She hummed at the contact, and mewled when he met his tongue with her now very erect nipples.

She ran her hands through his dark hair and whimpered as he lapped his tongue all over her boob and played with the other with his hand. She tugged his hair when he pinched it, choking out a loud moan.

“That’s...that’s really good.” she managed to say. Five grinned, taking in the look on her face as he lifted his head and studied her. He bit his wet lip.

“Yeah? Are you...are you wet though?” Five asked, a little nervous. 

Vanya nodded vigorously in reply, no longer shy enough to hold back her honesty.

Five said “Hm.” and pretended to think about her answer suspiciously. “I don’t believe you. Guess I’ll have to see for myself.”

He crawled back on the bed, facing her from the end of her feet. He placed a gentle hand on her knee, then realized how tightly her knees had snapped shut. He let out a chuckle.

“Hey, don’t hide from me.” He took Vanya’s knees and spread her legs wide. Vanya covered her face as Five’s hands crept up her thighs again. He stopped when he saw her. “Cmon, V.” he chuckled. “Don’t hide your cute face now.”

She peeked through her fingers at Five. “This is so overwhelming.” She squeaked.

He took his hands off of her. “Too overwhelming?”

“No! Just-“ she protested as she sat up. Their eyes exchanged a thousand words and feelings. “I really like it though.”

That seemed to be all the confirmation Five needed as he adjusted himself between her legs and spread them apart wider. Vanya bit her finger, feeling both nervous and delighted at the hands squeezing her upper thighs. 

They moved higher and higher until they reached the waistband of her underwear, where Five wrapped his fingers around it and pulled it down. Vanya blushed as Five slowly slid her panties down inch by tantalising inch. She wiggled her knees in impatience, whining.

“Okay, okay.” Five hummed as he fully removed the underwear and discarded it to the floor, then returning his hands to her pubis.

“Five-!” Vanya gasped as he softly slid his fingers into her vulva, beginning to rub around the area carefully. Vanya clutched her sheets, her breathing increasing.

Five worked her gently but mercilessly, stimulating her without a break. Whenever she began to make noises, he moved his hand faster, and whenever she calmed down, he moved on. Eventually he focussed on rubbing quick circles against her clit, which was met with cries of our pleasure.

He placed a kiss on her shaking thigh, and then another, higher. He kissed up the inside of her leg until he reached her wet pussy, where he placed a kiss too. Vanya melted at the touch, releasing a long, slow moan. “Yes...” she breathed shakily. “Yes, Five, please.”

Five couldn’t deny a plea that perfect, now could he? He licked a long stripe up her cunt, slow and steady even as Vanya’s knees spasmed.

He gave little kitten licks all around her vagina and then buried his his tongue deep into it, to which Vanya gasped and her body went rigid.

He continued to bury his tongue deep inside her until her voice got higher and higher until it reached incoherence. Vanya was past knowing what she was saying now. Her fluttering, beautiful eyelashes were sealed shut, her mind focussed solely on the feeling Five was creating.

Her whole stomach and thighs felt like they were fuzzy and warm. Her full, exposed chest was rising and falling rapidly and gracefully. And her cunt was quivering and wet. But her whole body was alight, floating and on edge. Every nerve in her body was reaching its point. And she felt like she was about to burst.

“Five...Five...Five! I’m going to-!” She began to cry. He murmured into her pussy in acknowledgement. She wrung the sheets in her fingers, pleasure building to its climax.

“Oh my god!” She yelled, coming with a broken cry. Her back arched off of the bed, her legs kicking. “Five!”

Five didn’t even stop lapping at her clit or running his fingers along her thighs as she came on his face. She rode out her orgasm, body shifting through the motions as she came down.

When she finally opened her eyes, she looked down at Five, wiping his chin and smiling. She blushed. “Oh! I’m so sorry Five!” She squeaked, closing her legs and sitting up to meet his face. She leaned over to her night table and grabbed a handkerchief to clean up his face.

He chuckled and breathed out “Its fine.”

“I’m sorry, I’m sorry. I’m sorry I’m so loud and needy and-“ she began to ramble guiltily. Five grabbed her face, making her stop. “I love all of those things, Vanya. You’re so pretty.”

Vanya smiled, melting into his touch. “Thank you.” She whispered. Five rubbed his thumb over lips, then dove in for a deep kiss. She tilted her head into it, grateful to finally kiss him again.

“Vanya” he moaned against her lips breathlessly. “You’re such a tease.”

He wrapped his arms around her waist. Hungrily he began to kiss deeper and run his hand up and down her back. His other returned to her chest, grabbing her still exposed breasts eagerly. She gasped into his mouth. Her hand grabbed his and helped him caress her.

“You hard?” She mumbled. He groaned. “Painfully so.”

She spared a glance downward, to see that he wasn’t lying. His dick was a stiff tent in his shorts. Vanya suddenly got an urge to place her hand up on his knee.

Five looked down, biting his lip. “Can I?” Vanya asked, trying to meet Fives enchanting gaze through the sweep of his hair. He practically moaned “Yes.” in return.

Carefully, she cupped his dick her hand, which made Five groan and buck his hips. “Vanya.” He breathed.

She unzipped his shorts and began to palm him through his underwear. His breath hitched as he leaned back a little, eyes closing in pleasure.

Vanya took his dick out of his underwear, surprisingly big and stiff in her hand. She spit in her hand, hoping she was doing this right.

She grabbed hold of his dick, giving it a long stroke, that made Five moan. She began to stroke him, twisting her wrist and smiling at the way it made Five buck his hips. His breathing was getting faster.

“Faster...” He panted. She obeyed, beginning to take his dick faster in her hand, the slick sounds lewd and egging them both on.

Still increasing the pace, she leaned over to kiss him, muffling his pants. He bucked his hips again, moaning into her mouth. “Vanya! Feels so good!” He cried. 

Vanya broke away. She spit on her hand again, then paused. She licked her lips and looked down at his twitching, hard dick. Slowly she sunk her head down. 

When Five felt her hot breath on his member, he opened his eyes, gasping. When she looked up at him, he nodded.

Vanya licked up his dick, holding it in place with her other hand. Five sighed sweetly, running his hands through her hair gently.

She licked her lips again once more before inching the cock into her throat. When she reached the base, she slid it out, then back in. Beginning to build up a rhythm, she unwaveringly began to speed up.

“Fuck, Vanya.” he choked out. “You’re so perfect.” 

Suddenly, Vanya went all the way down, hitting almost the back of her throat with the head of his dick. She choked slightly, and Five cried, tugging on her hair.

Vanya gasped around him, pulling up. “Oh-!”

Five quickly recoiled. “Vanya, are you okay? I’m sorry, I didn’t mean to I-“

“No! Do it again!” she squeaked. “I-I liked it!”

Five gently wrapped his fingers into Vanya’s long hair, and guided her head up and down his shaft. She moaned when he pulled at her hair, which sent vibrations through his dick and put him on edge.

With her head and her hand both working up and down his twitching dick, Five moaned out. “Vanya, I’m gonna come-“ he managed.

She willed herself to stop sucking, releasing her mouth from his dick. Five whined. 

“Do you want to come on my tits?” she whispered lewdly. Five’s eyes widened and he nodded vigorously.

She smiled and moved her hair out of the way, leaving her chest exposed. She blushed, but didn’t look away as she watched Five grab his own dick and start furiously stroking himself up and down. 

He sat up on his knees, his face contorted as he clearly neared release.

“Wait,” she breathed out. “Come on my face too.” 

She opened her mouth, tongue sticking out and slightly closing her eyes. From the pink coating her cheeks to her glassy, half lidded eyes, to her pretty lips now open in desperation from his come, it was all too much, and Five came.

Ropey spurts of white painted Vanya from her chin to her naked breasts. Five cried, relishing in the sight of coming all over her beautiful body. Coating her. Defiling her. 

When he was spent, he began to register the scene. “Oh, Vanya, you’re so good for me.” he said with a tone that radiated apology.

He then took the handkerchief, half soaked already in Vanya’s come, and cleaned up her mouth and his seed all over her tits. He made sure to take his time feeling her as he cleaned her up.

“Five...thank you.” She hummed, Watching him clean her.

He grinned and pecked her on the lips. “No, thank you. That was great.”

She murmured a sound of agreement. “We’ll have to do this again sometime.”


End file.
